Experimental study demonstrates photoinduced coupling of unactivated alkanes with glycine esters, highlighting a sustainable catalytic route to non-canonical amino acids.
Key Points
To develop a mild and sustainable photochemical approach for direct C(sp3)–C(sp3) cross-coupling between unactivated alkanes and glycine esters to synthesize non-canonical amino acid derivatives.
Coupled N-phenylglycine esters with diverse unactivated alkanes, including cyclohexane, cyclopentane, and adamantane, under 390 nm LED irradiation at room temperature.
Utilized copper(II) acetate as the catalyst and tert-butyl hydroperoxide as the terminal oxidant in the presence of various functional groups.
Conducted mechanistic investigations and demonstrated process scalability via gram-scale synthesis.
Generated a broad series of α-alkylated glycine derivatives with product yields reaching up to 89%.
Successfully scaled the photoredox protocol to a gram-scale synthesis, isolating the desired amino acid derivative in 69% yield.
Elucidated a radical pathway driven by single-electron transfer and alkoxy-mediated hydrogen atom transfer.